This study examined whether school engagement was protective with regard to externalizing behaviors, gang involvement, sexual debut, and unsafe sexual behaviors among African American adolescent males. Self-administered surveys were administered to 219 male students from an urban Chicago high school. Controlling for age and socioeconomic status, higher school engagement levels were associated with lower rates of aggressive behaviors, lower levels of gang involvement, delay of sexual debut, and lower levels of unsafe sexual behaviors. Findings support the development of school-based interventions designed to promote student–teacher bonds, academic performance, and after-school activities for African American youth.